Lithium hydroxide, monohydrate → 3-[3-(1,2-benzisoxazol-3-ylmethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]hexanoic acid

HRID 1747358Notes

Reaction equation

HRID 1747358 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][N:21]=2)[C:11]1=[O:29])[CH2:7][CH2:8][CH3:9])C.O.[OH-].[Li+]>C1COCC1.O>[O:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:30])=[O:3])[C:11]2=[O:29])=[N:21]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 594973183-(3-1,2-Benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester

Product 1

HCID 594973363-[3-(1,2-benzisoxazol-3-ylmethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]hexanoic acidYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(3-1,2-benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester (70 mg, 0.17 mmol) in THF (5 ml) and water (0.5 ml) was added lithium hydroxide monohydrate (22 mg, 0.52 mmol). Upon complete consumption of the starting material, the reaction was concentrated to low volume and diluted with water (20 ml) and acetic acid (0.5 ml). The resulting heterogeneous mixture was stirred for 1 h after which time the precipitated product was collected via filtration. The solid was washed with water and dried on house vacuum at 40° C. (18 h, over P2O5) to give 52 mg (80%) of the desired product. LCMS (ESMS): m/z 380.41 (M+H+).

Workup

  1. customUpon complete consumption of the starting material
  2. concentrationthe reaction was concentrated to low volume
  3. additiondiluted with water (20 ml) and acetic acid (0.5 ml)
  4. filtrationwas collected via filtration
  5. washThe solid was washed with water
  6. dry with materialdried on house vacuum at 40° C. (18 h, over P2O5)

Sources & evidence

ORD record
ord-14f0d0e5e1cb4abebf0b04882c5f81f0
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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